4-Amino-3-chlorobenzoic acid → 4-amino-3-chloro-N-(1-ethyl-4-piperidyl)benzamide

HRID 2234479Notes

Reaction equation

HRID 2234479 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[Cl:11].[CH2:12]([N:14]1[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]1)[CH3:13].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][CH:17]2[CH2:18][CH2:19][N:14]([CH2:12][CH3:13])[CH2:15][CH2:16]2)=[O:8])=[CH:4][C:3]=1[Cl:11]

Participants

6

Reactant 4

HCID 172114-Amino-3-chlorobenzoic acidHCID 81531DiisopropylethylamineHCID 37349901-Ethylpiperidin-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 643214944-amino-3-chloro-N-(1-ethyl-4-piperidyl)benzamideYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-amino-3-chloro-benzoic acid (Fluorochem; 2.575 g, 15 mmol) and 1-ethylpiperidin-4-amine (Fluorochem; 2.12 g, 16.5 mmol) in DMF (50 mL), was added DIPEA (5.2 mL, 30 mmol). The mixture was cooled with an ice-bath. HATU (6.27 g), added and the reaction mixture stirred at ambient temperature for 18 hours. The solvent was evaporated and the residue partitioned between saturated aqueous sodium bicarbonate solution (100 mL), and Ethyl Acetate (4×50 mL). The organic extracts were washed with brine (2×75 ml), dried over anhydrous Magnesium sulphate, filtered, and the solvent evaporated to give the crude product as a gum, which was triturated with ether to yield the title compound as a tan solid (3.54 g, 84%).

Workup

  1. temperatureThe mixture was cooled with an ice-bath
  2. customThe solvent was evaporated
  3. customthe residue partitioned between saturated aqueous sodium bicarbonate solution (100 mL), and Ethyl Acetate (4×50 mL)
  4. washThe organic extracts were washed with brine (2×75 ml)
  5. dry with materialdried over anhydrous Magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customto give the crude product as a gum, which
  9. customwas triturated with ether

Sources & evidence

ORD record
ord-dd648796d643462899719bf9fc1572c3
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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